2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → ethyl 4-(3-chlorophenyl)-1-ethyl-6-methyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate

HRID 2373213Notes

Reaction equation

HRID 2373213 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:12]([CH3:19])[NH:11][C:10]3[N:20]([CH2:23][CH3:24])[N:21]=[CH:22][C:9]2=3)[CH:5]=[CH:6][CH:7]=1.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.C([O-])(O)=O.[Na+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:12]([CH3:19])[N:11]=[C:10]3[N:20]([CH2:23][CH3:24])[N:21]=[CH:22][C:9]=23)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 516892Sodium BicarbonateHCID 1362379411h-Pyrazolo[3,4-b]pyridine-5-carboxylic acid,4-(3-chlorophenyl)-1-ethyl-4,7-dihydro-6-methyl-,ethyl ester

Product 1

HCID 69182036ethyl 4-(3-chlorophenyl)-1-ethyl-6-methyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylateYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 4-(3-chlorophenyl)-1-ethyl-6-methyl-4,7-dihydro-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (135 mg) in THF (3 ml) was added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (97.5 mg) and the reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was poured into saturated NaHCO3 and extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with a mixture of EtOAc and n-hexane (1:5) to give ethyl 4-(3-chlorophenyl)-1-ethyl-6-methyl-1H-pyrazolo[3,4-b]pyridine-5-carboxylate (47 mg) as colorless oil.

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel eluting with a mixture of EtOAc and n-hexane (1:5)

Sources & evidence

ORD record
ord-f503d19df8ce42ae9453ebf911c41cdc
Source dataset
uspto-grants-2008_12
Patent number
US07459451B2

Reaction notes

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